WO2014176254A4 - Seal compatibility additive to improve fluoropolymer seal compatibility of lubricant compositions - Google Patents

Seal compatibility additive to improve fluoropolymer seal compatibility of lubricant compositions Download PDF

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Publication number
WO2014176254A4
WO2014176254A4 PCT/US2014/034983 US2014034983W WO2014176254A4 WO 2014176254 A4 WO2014176254 A4 WO 2014176254A4 US 2014034983 W US2014034983 W US 2014034983W WO 2014176254 A4 WO2014176254 A4 WO 2014176254A4
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WIPO (PCT)
Prior art keywords
lubricant composition
new
amine compound
group
additive
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PCT/US2014/034983
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French (fr)
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WO2014176254A1 (en
Inventor
Kevin Desantis
Michael Hoey
David Chasan
Stephen Jones
Al JUNG
Phil RABBAT
Original Assignee
Basf Se
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Publication date
Application filed by Basf Se filed Critical Basf Se
Priority to MX2015014770A priority Critical patent/MX2015014770A/en
Priority to JP2016510738A priority patent/JP6293265B2/en
Priority to EP14787924.1A priority patent/EP2989186A4/en
Priority to CA2909821A priority patent/CA2909821A1/en
Priority to AU2014257238A priority patent/AU2014257238A1/en
Priority to RU2015149918A priority patent/RU2015149918A/en
Priority to BR112015026615A priority patent/BR112015026615A2/en
Priority to KR1020157032908A priority patent/KR20160003716A/en
Priority to CN201480030944.1A priority patent/CN105247024B/en
Publication of WO2014176254A1 publication Critical patent/WO2014176254A1/en
Publication of WO2014176254A4 publication Critical patent/WO2014176254A4/en

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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/06Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
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    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/04Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic halogen-containing compound
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    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M169/00Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
    • C10M169/04Mixtures of base-materials and additives
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
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    • C10M2207/00Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02Hydroxy compounds
    • C10M2207/023Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
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    • C10M2211/00Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/02Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only
    • C10M2211/022Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen and halogen only aliphatic
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064Di- and triaryl amines
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    • C10M2215/22Heterocyclic nitrogen compounds
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
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    • C10M2215/222Triazines
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    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/22Heterocyclic nitrogen compounds
    • C10M2215/223Five-membered rings containing nitrogen and carbon only
    • C10M2215/224Imidazoles
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    • C10M2215/26Amines
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    • C10M2215/28Amides; Imides
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/041Triaryl phosphates
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/043Ammonium or amine salts thereof
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/045Metal containing thio derivatives
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04Phosphate esters
    • C10M2223/047Thioderivatives not containing metallic elements
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    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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    • C10M2223/049Phosphite
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    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/09Characteristics associated with water
    • C10N2020/097Refrigerants
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    • C10N2020/101Containing Hydrofluorocarbons
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    • C10N2030/04Detergent property or dispersant property
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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Sealing Material Composition (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

This disclosure is directed to an additive package for a lubricant composition that provides improved compatibility with fluoropolymer seals. The additive package comprises a seal compatibility additive. The disclosure is also directed to a lubricant composition comprising a base oil and a seal compatibility additive. The seal compatibility additive improves the compatibility with fluoropolymer seals of the resultant lubricant composition.

Claims

AMENDED CLAIMS
received by the International Bureau on 31 October 2014 (31.10.2014)
What is claimed is:
1. (Currently Amended) An additive package for a lubricant composition that provides improved compatibility with fluoropoiymer seals, said additive package comprising:
a seal compatibility additive comprising at least one halogen atom selected from the group consisting of fluorine, bromine, iodine, and combinations thereof, and
an acyclic hydrocarbon backbone comprising at least one carbon atom, wherein said at least one halogen atom is bonded to said at least one carbon atom in said acyclic hydrocarbon backbone; and
an anti-wear agent comprising phosphorous.
2. (Currently Amended) The additi ve package of claim 1 further comprising an amine compound.
3. (Currently Amended) The additive package of claim 1 wherein said seal compatibility additive comprises an alkyl haiide compound having a general formula:
Figure imgf000002_0001
where n 1, I<m<(2n +2), and X is said halogen atom selected from the group consisting of fluorine, bromine, iodine, and combinations thereof.
4. (Original) The additive package of claim 2 wherein said amine compound comprises a sterically hindered amine compound.
5. (Original) The additive package of claim 2 wherein said amine compound comprises a sterically hindered amine compound having a general formula (Vlll):
64
Figure imgf000003_0001
wherein each R3 is independently a hydrogen atom or a hydrocarbyi group having from i to 17 carbon atoms;
wherein at least two groups designated by RJ are an alkyl group; and
wherein each R* is independently a hydrogen atom or a hydrocarbyi group having from 1 to 17 carbon atoms.
6, (Original) The additive package of claim 2 wherein said amine compound comprises an amine dispersant
7, (Cancelled)
8, (Cancelled)
9, (Currently Amended) A lubricant composition that provides improved compatibility with fluoropolymer sea!s, said lubricant composition comprising:
a base oil;
a seal compatibility additive comprising at least one halogen atom selected from the group consisting of fluorine, bromine, iodine, and combinations thereof, and
an acyclic hydrocarbon backbone comprising at least one carbon atom, wherein said at least one ha!ogen atom is bonded to said at least one carbon atom in said acyclic hydrocarbon backbone: and
an anti-wear agent comprising phosphorous.
65
10. (Currenily Amended) The lubricant composition of claim 9 further comprising an amine compound.
1 1. (Currenily Amended) The lubricant composition of claim 9 wherein said seal compatibility additive comprises an alkyl halide compound having a general formula: where n > 1, 3 <m<(2n +2), and X is said halogen atom selected from the group of fluorine, bromine, iodine, and combinations thereof.
12. (Cancelled)
13. (Original) The lubricant composition of claim 10 wherein said amine compound comprises a sterically hindered amine compound having a genera! formula (Vifi):
Figure imgf000004_0001
fYffl); wherein each R"' is independently a hydrogen atom or a hydrocarbyi group having from 1 to 17 carbon atoms;
wherein at least two groups designated by R3 are an alkyl group; and
wherein each R4 is independently a hydrogen atom or a hydrocarbyi group having from 1 to 17 carbon atoms.
14. (Original) The lubricant composition of claim 10 wherein said amine compound is present in said lubricant composition in an amount ranging from 0.1 to 10 wt.% based on a total weight of said 1 ubriears t composition .
66
15. (Orlgmal) The lubricant composition of claim 10 wherein said amine compound comprises an amine dispersant.
16. (Cancelled)
17. (Cancelled)
18. (Cancelled)
19. (Original) The lubricant composition of claim 9 having a fluoropoiyrner seal compatibility such that a f!uoropo!ymer seal submerged in said lubricant composition exhibits a change in elongation of from - 60 to 0% or a change in tensile strength of from -SO to 10%, when tested according to CEC L-39- T96.
20. (Currently Amended) A method of lubricating a system comprising a fluoropoiyrner seal, said method comprising:
providing a lubricant composition which comprises a base oil, an anti-wear agent comprising phosphorous, and a seal compatibility additive;
wherein the seal compatibility additive comprises at least one halogen atom selected from the group consisting of fluorine, bromine, iodine, and combinations thereof; and
an acyclic hydrocarbon backbone comprising at least one carbon atom, wherein said at least one halogen atom is bonded to said at least one carbon atom in said acyclic hydrocarbon backbone;
and
contacting the fluoropoiyrner seal with die lubricant composition.
21. (New) The additive package of claim 1 wherein said anti-wear agent comprising phosphorous comprises a dihydrocarbyl dithiophosphate salt.
22. (New) The lubricant composition of claim 9 wherein said anti-wear agent comprising phosphorous comprises a dihydrocarbyl dithiophosphate salt.
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23. (New) The lubricant composition of claim 9 wherein said anti-wear agent comprising phosphorous is present in said lubricant composition in an amount ranging from 0.1 to 10 t% based on a total weight of said lubricant composition.
24. (New) An additive package for a lubricant composition that provides improved compatibility with fluoropolymer seals, said additive package comprising:
a seal compatibility additive comprising at least one halogen atom selected iron) the group consisting of fluorine, bromine, iodine, and combinations thereof, and
an acyclic hydrocarbon backbone comprising at least one carbon atom, wherein said at least one halogen atom is bonded to said at least one carbon atom in said acyclic hydrocarbon backbone; and
a phenolic antioxidant,
25. (New) The additi ve package of claim 24 wherein said phenolic antioxidant is .selected from the group consisting of 2,6-d i-tert-butyl-4-ixiethyiphenol, 2-tert-butyl-4,6-di.methylphenol, 2,6-di-iert-butyW- eihyiphenol, 2,6-di-tert-butyl-4-n-butyiphe«oL 256-di-tert-b«tyl-4-isobutylphenol, 2,6-dicyclopentyl- 4-methyl henol, 2-(a~rocthyicyclohexyl)-4,6-dimethyiphenoi, 2,6-dioetadecyl-4-roethylphenol, 2,4,6- tricyclohexylphenol, 2,6-di-tert-biityl-4-«iethoxymethylphenol, 2,6-di-nonyl-4-niethylpbenoI, 2,4- dimethyi-6( 1 '-methyiundec- 1 '-yl)phenol, 2,4-dimethyi-6-( i -methylheptadee- 1 '~yi)phenol, 2,4- dijnethyi-6-(] '-methyltridec-r-yl)pbenoi, and combinations thereof.
26. (New) The additive package of claim 24 wherein said seal compatibility additive comprises an alkyl haiide compound having a general formula: where n > 1 , l<m<(2n +2), and X is said halogen atom selected from the group consisting of fluorine, bromine, iodine, and combinations thereof.
27. (New) The additive package of claim 24 further comprising an amine compound. 28, (New) The additive package of claim 27 wherein said amine compound comprises a sterically hindered amine compound having a general formula (ΥΠΙ):
Figure imgf000007_0001
wherein each R3 is independently a hvchOgen atom or a hydrocarbyl group having from 1 to 17 carbon atoms;
wherein at least two groups designated by RJ are an alkyl group; and
wherein each R4 is independently a hydrogen atom or a hydrocarbyl group having from 1 to 17 carbo atoms.
29. (New) The additive package of claim 27 wherein said amine compound comprises an amine dispersant.
30, (New) The additive package of any one of claims 24-29 further comprising an anti-wear agent comprising phosphorous.
33 , (New) A lubricant composition that provides improved compatibility with fluoropolymer seals, said lubricant composition comprising;
a base oii; and
a seal compatibility additive comprising at least one halogen atom selected from the group consisting of fluorine, bromine, iodine, and combinations thereof, and
an acyclic hydrocarbon backbone comprising at least one carbon atom. wherein said at least one halogen atom is bonded to said at least one carbon atom in said acyclic hydrocarbon backbone; and
a phenolic antioxidant.
(New) The lubricant composition of claim 33 wherein said seal compatibility additive comprises an alky! halide compound having a genera! formula:
Figure imgf000008_0001
where n > 1 , !<m<(2n +2), and X is said halogen atom selected from the group of fluorine, bromine, iodine, and combinations thereof,
33. (New) The lubricant composition of claim 31 further comprising an amine compound.
34. (New) The lubricant composition of claim 33 wherein said amine compound comprises a steriea!ly hindered amine compound,
35. (New) The lubricant composition of claim 33 wherein said amine compound comprises a sterically hindered amine compound having a general formula (V!il):
Figure imgf000008_0002
fVfii): wherein each R"' is independently a hydrogen atom or a hydrocarbyl group having from I to 17 carbon atoms;
wherein at least two groups designated by R3 are an alkyl group; and
wherein each R4 is independently a hydrogen atom or a hydrocarbyl group having from 3 to 17 carbon atoms.
36. (New) The lubricant composition of claim 33 wherein said amine compound is present in said lubricant composition in an amount ranging from 0, 3 to 10 wL¾ based on a total weight of said lubricant composition.
37. (New) The lubricant composition of claim 33 wherein said amine compound comprises an amine dispersani,
38. (New) The lubricant composition of claim 31 having a fluoropoiymer seal compatibility such that a fluoropolymer seal submerged in said lubricant composition exhibits a change in elongation of from - 60 to 10% or a change in tensile strength of from -50 to 10%, when tested according to CEC L-39- T96.
39. (New) The lubricant composition of claim 31 wherein said phenolic antioxidant is selected from the group consisting of 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyi-4,6-d imethyf phenol, 2,6-di-tert- hutyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-buty!phenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6- dicycIopent l-4-methylphenol, 2-(a-methyicyclohex l)-4,6-dimechylphenoi, 2,6-dtoctadecyl-4- methylphenoi, 2,4,6-tricyclohexylpheno!, 2,6-di-tert-butyi-4-niethoxymethyiphenol, 2,6-di-nonyl-4- methylphenol, 2,4-dimethyl-0(r-methy]undec-l'-yl)phenol, 2,4-dimethyl-6-(r~methy!heptadec-r- yi)phenoi, 2,4-diniethy1~6-(i'-meihyltridec~r-y!)phenoL and combinations thereof.
40. (New) The lubricant composition of claim 31 wherein said phenolic antioxidant is present in said lubricant composition in an amount ranging from 0.0; to 5 wt.% based on a tola! weight of said lubricant composition.
41. (New) The lubricant composition of any one of claims .31 -40 further comprising anti-wear agent comprising phosphorous.
42. (New) A method of lubricating a system comprising a fluoropolymer seal, said method comprising: providing a lubricant composition which comprises a base oil, a phenolic antioxidant, and a seal compatibility additive;
71 wherein the seal compatibility additive comprises at least one halogen atom selected from the grasp consisting of fluorine, bromine, iodine, and combinations thereof, and
an acyclic hydrocarbon backbone comprising at least one carbon atom, wherein the at least one halogen atom is bonded to the at least one carbon atom in the acyclic hydrocarbon backbone; contacting the fluoropolymer seal with the lubricant composition.
72
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EP14787924.1A EP2989186A4 (en) 2013-04-22 2014-04-22 Seal compatibility additive to improve fluoropolymer seal compatibility of lubricant compositions
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AU2014257238A AU2014257238A1 (en) 2013-04-22 2014-04-22 Seal compatibility additive to improve fluoropolymer seal compatibility of lubricant compositions
RU2015149918A RU2015149918A (en) 2013-04-22 2014-04-22 ADDITIVE FOR IMPROVEMENT OF COMPATIBILITY WITH SEALS FOR IMPROVEMENT OF COMPATIBILITY OF LUBRICANT COMPOSITIONS WITH FLUOR POLYMER SEALS
BR112015026615A BR112015026615A2 (en) 2013-04-22 2014-04-22 additive packaging for a lubricant composition, lubricant composition, and method for lubricating a system
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